Structure Database (LMSD)

Common Name
AT-Resolvin D3
Systematic Name
4S,11R,17R- trihydroxy-5Z,7E,9E,13Z,15E,19Z-docosahexaenoic-acid
Synonyms
  • AT-RvD3
LM ID
LMFA04030008
Formula
Exact Mass
Calculate m/z
376.224976
Sum Composition
Status
Curated

Classification

Biological Context

17(R)-Resolvin D3 (17(R)-RvD3) is an aspirin-triggered epimer of resolvin D3 .1 It is produced from docosahexaenoic acid (DHA) by COX-2 in the presence of aspirin via a 17(R)-hydroperoxy DHA (17(R)-HDHA) intermediate and has been found in mouse inflammatory exudates.1,2 17(R)-RvD3 reduces transmigration of isolated human polymorphonuclear cells (PMNs) and induces efferocytosis of apoptotic PMNs by macrophages.2 17(R)-RvD3 (10 ng/animal) reduces transmigration of neutrophils into the peritoneal cavity, as well as decreases the levels of IL-6 and increases the levels of IL-10 in inflammatory exudate in a mouse model of zymosan-induced peritonitis. It activates GPR32 in a β-arrestin reporter assay and increases phagocytosis to a greater degree in CHO cells overexpressing GPR32 compared to mock-transfected cells. 17(R)-RvD3 increases phagocytosis of etoposide-generated tumor cell debris by monocyte-derived macrophages in H460 human lung carcinoma cells in a concentration-dependent manner.3 It also inhibits tumor growth in a mouse model of Lewis lung carcinoma when administered at a dose of 0.6 µg/kg per day.

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Resolvin D3 and aspirin-triggered resolvin D3 are potent immunoresolvents.,
Chem Biol, 2013
Pubmed ID: 23438748

String Representations

InChiKey (Click to copy)
QBTJOLCUKWLTIC-AXRBAIMGSA-N
InChi (Click to copy)
InChI=1S/C22H32O5/c1-2-3-7-12-19(23)14-10-6-11-15-20(24)13-8-4-5-9-16-21(25)17-18-22(26)27/h3-11,13-14,16,19-21,23-25H,2,12,15,17-18H2,1H3,(H,26,27)/b5-4+,7-3-,11-6-,13-8+,14-10+,16-9-/t19-,20+,21-/m1/s1
SMILES (Click to copy)
C(CC[C@H](O)/C=C\C=C\C=C\[C@H](O)C/C=C\C=C\[C@H](O)C/C=C\CC)(=O)O

Other Databases

CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 27
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 414.63
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 4.32
Molar Refractivity 110.79

Admin

Created at
-
Updated at
2nd Dec 2024